DE1227445C2 - Verfahren zur Herstellung von Harnstoffderivaten - Google Patents
Verfahren zur Herstellung von HarnstoffderivatenInfo
- Publication number
- DE1227445C2 DE1227445C2 DE1962C0032221 DEC0032221A DE1227445C2 DE 1227445 C2 DE1227445 C2 DE 1227445C2 DE 1962C0032221 DE1962C0032221 DE 1962C0032221 DE C0032221 A DEC0032221 A DE C0032221A DE 1227445 C2 DE1227445 C2 DE 1227445C2
- Authority
- DE
- Germany
- Prior art keywords
- bromine
- melting point
- compounds
- chlorophenyl
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000003672 ureas Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
- 229910052794 bromium Inorganic materials 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 230000031709 bromination Effects 0.000 description 7
- 238000005893 bromination reaction Methods 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- -1 organic Chemical compound 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZARXGSLQERUNSR-UHFFFAOYSA-N 1-butyl-3-(3-chlorophenyl)-1-methylurea Chemical compound CCCCN(C)C(=O)NC1=CC=CC(Cl)=C1 ZARXGSLQERUNSR-UHFFFAOYSA-N 0.000 description 1
- QLQDWOFJALEHSP-UHFFFAOYSA-N 3-(3-chlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC(Cl)=C1 QLQDWOFJALEHSP-UHFFFAOYSA-N 0.000 description 1
- SQXTYPWFGHQQMM-UHFFFAOYSA-N 3-(4-bromo-3-chlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 SQXTYPWFGHQQMM-UHFFFAOYSA-N 0.000 description 1
- ZAJBCCGJWLFTKH-UHFFFAOYSA-N 3-[(3-bromo-4-methoxyphenyl)methyl]-1h-imidazol-3-ium;chloride Chemical compound Cl.C1=C(Br)C(OC)=CC=C1CN1C=NC=C1 ZAJBCCGJWLFTKH-UHFFFAOYSA-N 0.000 description 1
- MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XVDWMONETMNKBK-UHFFFAOYSA-N calcium;dihypobromite Chemical compound [Ca+2].Br[O-].Br[O-] XVDWMONETMNKBK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WSSOFBRSFAPKKC-UHFFFAOYSA-N n-bromoformamide Chemical class BrNC=O WSSOFBRSFAPKKC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UEXZYUUKJQPTCQ-UHFFFAOYSA-N pyridin-1-ium;bromide;hydrobromide Chemical compound Br.Br.C1=CC=NC=C1 UEXZYUUKJQPTCQ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/38—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH533661A CH398543A (de) | 1961-05-06 | 1961-05-06 | Verfahren zur Herstellung von Harnstoffderivaten |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1227445B DE1227445B (de) | 1966-10-27 |
DE1227445C2 true DE1227445C2 (de) | 1973-10-04 |
Family
ID=4291866
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1962C0032221 Expired DE1227445C2 (de) | 1961-05-06 | 1962-05-04 | Verfahren zur Herstellung von Harnstoffderivaten |
DE1962C0026904 Expired DE1210793C2 (de) | 1961-05-06 | 1962-05-04 | Verfahren zur herstellung von harnstoffderivaten |
DE1793602A Expired DE1793602C3 (de) | 1961-05-06 | 1962-05-04 | N-O-ChloM-bromphenyO-K-methyl-K-methoxy-harnstoff. Ausscheidung aus: 1542724 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1962C0026904 Expired DE1210793C2 (de) | 1961-05-06 | 1962-05-04 | Verfahren zur herstellung von harnstoffderivaten |
DE1793602A Expired DE1793602C3 (de) | 1961-05-06 | 1962-05-04 | N-O-ChloM-bromphenyO-K-methyl-K-methoxy-harnstoff. Ausscheidung aus: 1542724 |
Country Status (7)
Country | Link |
---|---|
US (4) | US3288851A (enrdf_load_stackoverflow) |
BE (1) | BE662268A (enrdf_load_stackoverflow) |
CH (1) | CH398543A (enrdf_load_stackoverflow) |
DE (3) | DE1227445C2 (enrdf_load_stackoverflow) |
FR (1) | FR1325926A (enrdf_load_stackoverflow) |
GB (1) | GB965313A (enrdf_load_stackoverflow) |
OA (1) | OA01202A (enrdf_load_stackoverflow) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH398543A (de) * | 1961-05-06 | 1966-03-15 | Ciba Geigy | Verfahren zur Herstellung von Harnstoffderivaten |
DE1242936B (de) * | 1965-03-12 | 1967-06-22 | Schering Ag | Selektive Herbizide |
DE1542785A1 (de) * | 1965-07-24 | 1970-05-06 | Bayer Ag | Insekten- und milbenabweisende Mittel |
CH466943A (de) * | 1965-10-28 | 1968-12-31 | Sandoz Ag | Unkrautbekämpfung in Kulturen |
US3994714A (en) * | 1965-10-28 | 1976-11-30 | Sandoz Ltd. | Method for selective herbicidal treatment of barley cultures |
US3507899A (en) * | 1966-03-01 | 1970-04-21 | Basf Ag | Production of n-p-bromophenyl-n'-methyl-n'-methoxyurea |
US3497344A (en) * | 1966-11-15 | 1970-02-24 | United States Borax Chem | Herbicidal compositions and methods utilizing uramidobenzoate compounds |
CH488723A (de) * | 1967-12-27 | 1970-04-15 | Agripat Sa | Verfahren zur Herstellung von Thiadiazolyl-harnstoffen |
US3982922A (en) * | 1967-12-28 | 1976-09-28 | Velsicol Chemical Corporation | Herbicidal compositions containing furancarboxamides |
GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
GB1266172A (enrdf_load_stackoverflow) * | 1968-03-13 | 1972-03-08 | ||
US4686294A (en) * | 1968-12-20 | 1987-08-11 | Ciba-Geigy Corporation | 1,3,4-thiadiazolyl ureas and processes for controlling weeds and wild grasses therewith |
US3951641A (en) * | 1969-08-05 | 1976-04-20 | Ciba-Geigy Ag | Use of N-(4-isopropoxy-3-chlorophenyl)-N'-methyl-N'-methoxyurea for control of weeds in maize cultures |
US3806599A (en) * | 1970-04-22 | 1974-04-23 | Roussel Uclaf | Method for treating topical bacterial or fungal infections |
IL36718A0 (en) * | 1970-04-30 | 1971-06-23 | Ciba Geigy Ag | Herbicidal compositions containing phenylureas,certain new phenylureas and their preparation |
DE2033908B2 (de) * | 1970-07-08 | 1974-02-28 | Diamond Shamrock Corp., Cleveland, Ohio (V.St.A.) | Harnstoff-Derivate |
CA920835A (en) * | 1971-02-08 | 1973-02-13 | F. Adams Bobby | Method of regulating plant growth |
US3928600A (en) * | 1972-05-15 | 1975-12-23 | Chevron Res | N-polyhalovinylthiocarboxamides as nematocides |
US3771993A (en) * | 1972-05-15 | 1973-11-13 | Chevron Res | N-aryl-n-alkyl-n{40 -arylthio ureas as herbicides |
FR2187220B1 (enrdf_load_stackoverflow) * | 1972-06-09 | 1978-12-08 | Ciba Geigy Ag | |
US3901687A (en) * | 1973-08-31 | 1975-08-26 | Scott & Sons Co O M | Process for the selective control of weeds in kentucky bluegrass |
US3988294A (en) * | 1974-03-11 | 1976-10-26 | R. T. Vanderbilt Company, Inc. | Surface coating compositions containing antimicrobic ureas |
GB1476351A (en) * | 1974-04-17 | 1977-06-10 | Wilkinson Sword Ltd | Compounds having a physiological cooling effect and compo sitions containing them |
US4242273A (en) * | 1977-09-27 | 1980-12-30 | American Cyanamid Company | 4-(Monoalkylamino)benzoic acid amides and imidates |
US5003106A (en) * | 1983-07-19 | 1991-03-26 | American Cyanamid Company | Antiatherosclerotic ureas and thioureas |
FR2669926A1 (fr) * | 1990-11-29 | 1992-06-05 | Medgenix Group Sa | Ligands specifiques des recepteurs aux benzodiazepines peripheriques. |
EP2052609A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
DE102008037621A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
BE1026422B1 (nl) | 2018-07-02 | 2020-02-03 | Belchim Crop Prot N V | Synergetisch werkzame herbicidesamenstelling omvattende metobromuron en clomazon |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2653864A (en) * | 1951-12-26 | 1953-09-29 | Monsanto Chemicals | Method of destroying plants |
US2655534A (en) * | 1951-10-25 | 1953-10-13 | Du Pont | Preparation of n-aromatic-n'-aliphatic hydrocarbon ureas |
US2764478A (en) * | 1954-12-28 | 1956-09-25 | Du Pont | Weed control composition and method |
DE1102722B (de) * | 1959-04-18 | 1961-03-23 | Thomae Gmbh Dr K | Verfahren zur Herstellung von substituierten Harnstoffen |
FR1325926A (fr) * | 1961-05-06 | 1963-05-03 | Ciba Geigy | Procédé de préparation de dérivés de l'urée utilisables notamment pour lutter contre les mauvaises herbes |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2705195A (en) * | 1951-09-27 | 1955-03-29 | Du Pont | Herbicidal compositions and methods employing solutions of substituted ureas in monohydric phenols |
US2655444A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | 3-(halophenyl)-1, 1-dialkyl ureas and weed control compositions and methods |
US2655446A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | Chemical compositions and methods |
US2655447A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | Composition and method |
US2663729A (en) * | 1952-11-04 | 1953-12-22 | Du Pont | Haloarylhydroxyalkyl-ureas |
US2663730A (en) * | 1953-09-16 | 1953-12-22 | Ethyl Corp | N-alkyl-n'-(p-hydroxyphenyl) ureas |
BE529063A (enrdf_load_stackoverflow) * | 1953-10-13 | |||
US2913322A (en) * | 1955-12-29 | 1959-11-17 | Monsanto Chemicals | Halogen substituted carboxanilides |
US2960534A (en) * | 1957-06-11 | 1960-11-15 | Hoechst Ag | Nu-(chlorosubstituted aryl)-nu' methoxy-nu' methyl ureas |
US3079244A (en) * | 1957-06-14 | 1963-02-26 | Hoechst Ag | Herbicidal method |
NL233875A (enrdf_load_stackoverflow) * | 1957-12-05 | |||
GB973354A (en) * | 1960-10-31 | 1964-10-21 | Du Pont | Improvements in or relating to herbicidal compositions |
NL273695A (enrdf_load_stackoverflow) * | 1961-01-19 | |||
US3288586A (en) * | 1963-11-07 | 1966-11-29 | Du Pont | Herbicidal methods employing an addition compound of 3-(3, 4-dichlorophenyl)-1-methyl-1-methoxyurea and dodecylbenzenesulfonic acid |
-
1961
- 1961-05-06 CH CH533661A patent/CH398543A/de unknown
-
1962
- 1962-05-01 US US191442A patent/US3288851A/en not_active Expired - Lifetime
- 1962-05-04 DE DE1962C0032221 patent/DE1227445C2/de not_active Expired
- 1962-05-04 FR FR896446A patent/FR1325926A/fr not_active Expired
- 1962-05-04 DE DE1962C0026904 patent/DE1210793C2/de not_active Expired
- 1962-05-04 DE DE1793602A patent/DE1793602C3/de not_active Expired
- 1962-05-07 GB GB17518/62A patent/GB965313A/en not_active Expired
-
1964
- 1964-12-31 OA OA51383A patent/OA01202A/xx unknown
-
1965
- 1965-02-16 US US433155A patent/US3223721A/en not_active Expired - Lifetime
- 1965-04-08 BE BE662268A patent/BE662268A/fr unknown
-
1966
- 1966-04-19 US US543541A patent/US3497541A/en not_active Expired - Lifetime
-
1970
- 1970-06-22 US US48955A patent/US3692911A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2655534A (en) * | 1951-10-25 | 1953-10-13 | Du Pont | Preparation of n-aromatic-n'-aliphatic hydrocarbon ureas |
US2653864A (en) * | 1951-12-26 | 1953-09-29 | Monsanto Chemicals | Method of destroying plants |
US2764478A (en) * | 1954-12-28 | 1956-09-25 | Du Pont | Weed control composition and method |
DE1102722B (de) * | 1959-04-18 | 1961-03-23 | Thomae Gmbh Dr K | Verfahren zur Herstellung von substituierten Harnstoffen |
FR1325926A (fr) * | 1961-05-06 | 1963-05-03 | Ciba Geigy | Procédé de préparation de dérivés de l'urée utilisables notamment pour lutter contre les mauvaises herbes |
Also Published As
Publication number | Publication date |
---|---|
GB965313A (en) | 1964-07-29 |
DE1793602C3 (de) | 1974-03-07 |
BE662268A (enrdf_load_stackoverflow) | 1965-08-02 |
US3223721A (en) | 1965-12-14 |
CH398543A (de) | 1966-03-15 |
US3288851A (en) | 1966-11-29 |
OA01202A (fr) | 1969-01-25 |
DE1793602A1 (de) | 1972-08-31 |
US3497541A (en) | 1970-02-24 |
DE1210793B (de) | 1966-02-17 |
FR1325926A (fr) | 1963-05-03 |
DE1227445B (de) | 1966-10-27 |
DE1210793C2 (de) | 1976-01-29 |
US3692911A (en) | 1972-09-19 |
DE1793602B2 (de) | 1973-07-26 |
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